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This affluent, lake-filled suburb offers the anti–theme park experience just a few minutes east of downtown Orlando. There’s something decidedly European about strolling along its main shopping and dining street, Park Avenue, which is lined with cute little cafes and independent boutiques. Bringing further sophistication to the town is Rollins College, a private university with a stunning campus, and cultural attractions like the Charles Hosmer Museum, which houses the most comprehensive collection of Louis Comfort Tiffany glass works anywhere. Plan your visit around the farmers’ market, held every Saturday at the historic train depot in the center of town, or the nationally lauded Winter Park Sidewalk Arts Festival, which occurs every March.